Sodium Carbonate → HCID 68295187, compound

HRID 1184945Notes

Reaction equation

Br[C:2]1[N:7]=[C:6]([C:8]([NH:10][C@H:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[CH2:12][C:13]([OH:15])=[O:14])=[O:9])[CH:5]=[CH:4][C:3]=1[O:23][CH3:24].C([O-])([O-])=O.[Na+].[Na+]>CN(C=O)C.C1(B(O)O)C=CC=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[F:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[C@@H:11]([NH:10][C:8]([C:6]1[CH:5]=[CH:4][C:3]([O:23][CH3:24])=[C:2]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:7]=1)=[O:9])[CH2:12][C:13]([OH:15])=[O:14]

Participants

Conditions

Temperature: 100 °C

Procedure

50 mg (0.12 mmol) of (S)-3-[(6-Bromo-5-methoxy-pyridine-2-carbonyl)-amino]-3-(2-fluoro-phenyl)-propionic acid are dissolved in 3 ml of DMF, 120 mg (0.16 mmol, 1.35 eq) phenylboronic acid, 10 mg of bis(triphenylphosphine)palladium(II)chloride as catalyst and 1 ml of 1N Na2CO3 solution are added and the resulting mixture is heated to 100° C. for 6 hours. The mixture is filtrated via a pad of celite and subjected to preparative HPLC chromatography to yield 15 mg (31%) of product.

Workup

filtrationThe mixture is filtrated via a pad of celite

Sources & evidence

ORD record: ord-2107e43f292c4ee8afc8fe45d4b7b051
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08669370B2

Reaction notes

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