Sodium Bicarbonate → HCID 57898917, compound

HRID 911020Notes

Reaction equation

Br[C:2]1[C:3]([O:21][C:22]2[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=2[F:29])=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:13]=2)=[N:6][CH:7]=1.[N:30]1[CH:35]=[CH:34][CH:33]=[C:32](B(O)O)[CH:31]=1.C(=O)(O)[O-].[Na+]>COCCOC.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>[F:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([F:28])[C:22]=1[O:21][C:3]1[CH:4]=[C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[N:13]=2)[N:6]=[CH:7][C:2]=1[C:32]1[CH:31]=[N:30][CH:35]=[CH:34][CH:33]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Ethyl 3-(2-(5-bromo-4-(2,6-difluorophenoxy)pyridin-2-ylamino)thiazol-4-yl)propanoate (0.1932 mmol), pyridin-3-ylboronic acid (0.02850 g, 0.2319 mmol), Pd(PPh3)4 (0.02233 g, 0.01932 mmol), in DME (10 mL), and 2M sodium bicarbonate (2 mL) are combined and heated to 80° C. overnight. The reaction mixture is cooled and partitioned between CH2Cl2 and water. The combined organic layers are dried, filtered, and concentrated. The residue is purified by silica gel, eluting with 30-40% EtOAc in hexane, to afford ethyl 3-(2-(4-(2,6-difluorophenoxy)-3,3′-bipyridin-6-ylamino)thiazol-4-yl)propanoate.

Workup

temperatureThe reaction mixture is cooled
custompartitioned between CH2Cl2 and water
customThe combined organic layers are dried
filtrationfiltered
concentrationconcentrated
customThe residue is purified by silica gel
washeluting with 30-40% EtOAc in hexane

Sources & evidence

ORD record: ord-a9a3b53f21fe4e60aa18a4c3dc32a775
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08022222B2

Reaction notes

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