Potassium Carbonate → HCID 57812589, compound

HRID 912001Notes

Reaction equation

HRID 912001 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.OB(O)[C:26]1[S:30][C:29]([C:31]([OH:33])=[O:32])=[CH:28][CH:27]=1.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:26]3[S:30][C:29]([C:31]([OH:33])=[O:32])=[CH:28][CH:27]=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 27798075-Boronothiophene-2-carboxylic acidHCID 578127253-Bromo-7-[(R)-1-(2,6-dichloro-3-fluorophenyl)ethoxy]furo[3,2-c]pyridin-6-ylamine

Product 1

HCID 57812589HCID 57812589, 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-(dihydroxyboryl)thiophene-2-carboxylic acid (205 mg, 1.19 mmol), Pd(PPh3)4 (10.0 mg, 0.01 mmol), potassium carbonate (98.7 mg, 0.714 mmol) and 4:1 dioxane:water (4 mL) was heated in a microwave reactor at 100° C. for 6 h. The material was dry-loaded onto silica gel for column chromatography. The crude product was eluted with 20% MeOH/DCM. The fractions containing the product were concentrated in vacuo to afford the title compound as a white solid. 1H NMR (400 MHz, CD3OD): δ=1.90 (d, J=6.8 Hz, 3H), 6.54 (q, J=6.9 Hz, 1H), 7.22 (t, J=8.6 Hz, 1H), 7.31 (d, J=3.8 Hz, 1H), 7.41 (dd, J=9.0, 4.9 Hz, 1H), 7.53 (d, J=3.8 Hz, 1H), 7.92 (s, 1H), 8.27 (s, 1H).

Workup

  1. washThe crude product was eluted with 20% MeOH/DCM
  2. additionThe fractions containing the product
  3. concentrationwere concentrated in vacuo

Sources & evidence

ORD record
ord-a021214c3b6043178b3e486404a272ae
Source dataset
uspto-grants-2011_09
Patent number
US08022206B2

Reaction notes

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