Potassium Carbonate → HCID 59736765, compound

HRID 252853Notes

Reaction equation

HRID 252853 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14]([C:16]1[S:20][C:19]2[CH:21]=[CH:22][C:23](Br)=[CH:24][C:18]=2[CH:17]=1)=[O:15].B(O)(O)[C:27]1[CH:32]=[CH:31][CH:30]=[N:29][CH:28]=1.CC1C(P(C2C(C)=CC=CC=2)C2C(C)=CC=CC=2)=CC=CC=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.O>[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][CH:10]=[CH:11][CH:12]=2)=[CH:4][C:3]=1[NH:13][C:14]([C:16]1[S:20][C:19]2[CH:21]=[CH:22][C:23]([C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)=[CH:24][C:18]=2[CH:17]=1)=[O:15]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 80271Tri-o-tolylphosphineHCID 27343783-Pyridinylboronic acidHCID 59736687HCID 59736687, compound

Product 1

HCID 59736765HCID 59736765, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 18180031Water 1,2-dimethoxyethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a stirred solution of 261a (120 mg, 0.26 mmol) and pyridin-3-yl-3-boronic acid (123 mg, 0.34 mmol) in a 2:1 mixture of DME-water (9 mL), was added Pd(PPh3)4 (22 mg, 0.018 mmol), tri-o-toly phosphine (6 mg, 0.018 mmol) and potassium carbonate (109 mg, 0.79 mmol). The solution was degassed with N2 for 5 minutes and then heated at 80° C. for 15 hours. Water (50 mL) was added and the mixture was extracted with ethyl acetate (2×40 mL). The organic layer was separated, dried with sodium sulfate and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel, eluent ethyl acetate. A subsequent trituration was performed with DCM for 15 minutes to yield 262 as a white solid (80 mg, 67% yield). 1H NMR: (DMSO) δ 10.09 (s, 1H), 8.99 (dd, J=2.3, 0.8 Hz, 1H), 8.58 (dd, J=4.7, 1.6 Hz, 1H), 8.38 (s, 1H), 8.33 (d, J=1.4 Hz, 1H), 8.17 (ddd, J=9.6, 3.9, 1.8 Hz, 1H), 7.83 (dd, J=8.5, 1.8 Hz, 1H), 7.53-7.50 (m, 2H), 7.46 (d, J=2.2 Hz, 1H), 7.34 (dd, J=5.1, 1.2 Hz, 1H), 7.31 (dd, J=8.2, 2.2 Hz, 1H), 7.25 (dd, J=3.5, 1.2 Hz, 1H), 7.03 (dd, J=5.1, 3.7 Hz, 1H), 6.81 (d, J=8.4 Hz, 1H), 5.74 (s, 2H).

Workup

  1. customThe solution was degassed with N2 for 5 minutes
  2. additionWater (50 mL) was added
  3. extractionthe mixture was extracted with ethyl acetate (2×40 mL)
  4. customThe organic layer was separated
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue was purified by flash chromatography on silica gel, eluent ethyl acetate

Sources & evidence

ORD record
ord-847d8143bc694c27ae5c939802ac2e73
Source dataset
uspto-grants-2011_01
Patent number
US07868205B2

Reaction notes

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