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Potassium Carbonate → 3-(1,3-benzothiazol-2-yl)-5-(1H-indol-2-yl)pyridin-2-amine

HRID 1926370
Notes
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Reaction equation

HRID 1926370 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14](Br)[CH:15]=1.C([N:25]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[CH:27]=[C:26]1B(O)O)(OC(C)(C)C)=O.C(=O)([O-])[O-].[K+].[K+]>O1CCOCC1.O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH2:17])=[N:12][CH:13]=[C:14]([C:26]2[NH:25][C:33]3[C:28]([CH:27]=2)=[CH:29][CH:30]=[CH:31][CH:32]=3)[CH:15]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27733021-(tert-Butoxycarbonyl)indole-2-boronic Acid (contains varying amounts of Anhydride)HCID 67389127HCID 67389127, compound

Product 1

HCID 675211743-(1,3-benzothiazol-2-yl)-5-(1H-indol-2-yl)pyridin-2-amine

Reagents, catalysts & solvents 3

HCID 44119782
Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)
Catalyst
HCID 962WaterSolvent
HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-benzothiazol-2-yl-5-bromopyridin-2-ylamine (BB7) (25 mg, 0.080 mmol), 1-Boc-indole-2-boronic acid (40 mg, 0.20 mmol) and potassium carbonate (34 mg, 0.24 mmol) in 1,4-dioxane (1.4 mL) and H2O (0.5 mL) was degassed and refilled with argon (3×) prior to the addition of Pd(dppf)Cl2 (6 mg, 0.01 mmol). The reaction mixture was degassed and refilled with argon (2×) and left to stir at 100° C. in the microwave reactor for 30 min. Then, the mixture was passed through PL-Thiol MP SPE resin and concentrated in vacuo. The residual oil was partitioned between DCM and H2O. The combined organic layers were treated with brine, dried over anhydrous Na2SO4 and concentrated in vacuo. The resulting Boc-protected intermediate was left to stir in (1:1) DCM:TFA mixture (1.0 mL) at rt for 15 min. Purification via MDP afforded the title compound as a yellow solid. MS (ES+): m/z=343.08 (100) [MH+]. HPLC: tR=4.00 min (ZQ3, polar—5 min).

Workup

  1. customwas degassed
  2. additionrefilled with argon (3×)
  3. customThe reaction mixture was degassed
  4. additionrefilled with argon (2×)
  5. waitleft
  6. concentrationconcentrated in vacuo
  7. customThe residual oil was partitioned between DCM and H2O
  8. additionThe combined organic layers were treated with brine
  9. dry with materialdried over anhydrous Na2SO4
  10. concentrationconcentrated in vacuo
  11. waitwas left
  12. stirringto stir in (1:1) DCM
  13. waitTFA mixture (1.0 mL) at rt for 15 min
  14. customPurification via MDP

Sources & evidence

ORD record
ord-2f0c4f6180ab4d188062921805e22f1d
Source dataset
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08178668B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes