Potassium Carbonate → HCID 57812491, compound

HRID 912002Notes

Reaction equation

HRID 912002 reaction equation
Br[C:2]1[C:6]2[CH:7]=[N:8][C:9]([NH2:23])=[C:10]([O:11][C@@H:12]([C:14]3[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=3[Cl:22])[CH3:13])[C:5]=2[O:4][CH:3]=1.[CH:24]([C:26]1[S:30][C:29](B(O)O)=[CH:28][CH:27]=1)=[O:25].C(=O)([O-])[O-].[K+].[K+].O1CCOCC1>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.O>[NH2:23][C:9]1[N:8]=[CH:7][C:6]2[C:2]([C:29]3[S:30][C:26]([CH:24]=[O:25])=[CH:27][CH:28]=3)=[CH:3][O:4][C:5]=2[C:10]=1[O:11][C@@H:12]([C:14]1[C:19]([Cl:20])=[CH:18][CH:17]=[C:16]([F:21])[C:15]=1[Cl:22])[CH3:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 312751,4-DioxaneHCID 27734305-Formyl-2-thiopheneboronic acidHCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 57812491HCID 57812491, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

A mixture of 3-bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)-ethoxy]-furo[3,2-c]pyridine-6-ylamine (100.0 mg, 0.238 mmol), 5-formyl-2-thiopheneboronic acid (55.7 mg, 0.357 mmol), Pd(PPh3)4 (10.0 mg, 0.01 mmol), potassium carbonate (98.7 mg, 0.714 mmol) and 4:1 dioxane:water (10 mL) was heated to 90° C. overnight. The material was concentrated in vacuo, redissolved in DCM and transferred to a separatory funnel, extracting with sat. NaHCO3. The organic layer was dry-loaded onto silica gel for column chromatography, eluting with 2% MeOH/DCM. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a yellow solid. 1H NMR (400 MHz, CD3OD): δ=1.90 (d, J=6.8 Hz, 3H), 6.53 (q, J=6.7 Hz, 1H), 7.20-7.25 (m, 1H), 7.41 (dd, J=8.8, 4.8 Hz, 1H), 7.59 (d, J=3.8 Hz, 1H), 7.94 (d, J=4.0 Hz, 1H), 8.13 (s, 1H), 8.28 (s, 1H), 9.89 (s, 1H). MS (ES+): m/z 450.92 (100) [MH+]. HPLC: tR=3.75 min (ZQ3, polar—5 min).

Workup

  1. concentrationThe material was concentrated in vacuo
  2. dissolutionredissolved in DCM
  3. customtransferred to a separatory funnel
  4. extractionextracting with sat. NaHCO3
  5. washeluting with 2% MeOH/DCM
  6. additionThe fractions containing the pure product
  7. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-9ff496c89f114bd7907a09d4f26338c9
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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