Ammonia → HCID 86700787, compound

HRID 2406522Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:26])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@H:15]3[C:23]4[C:18](=[C:19](Br)[CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1.[Cl-].[Cl:28][C:29]1[CH:34]=[CH:33][C:32]([CH2:35][Zn+])=[CH:31][N:30]=1.Cl.N>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.O1CCCC1>[CH3:1][O:2][C:3](=[O:26])[CH2:4][C@H:5]1[C:9]2[CH:10]=[CH:11][C:12]([O:14][C@:15]3([CH2:35][C:32]4[CH:31]=[N:30][C:29]([Cl:28])=[CH:34][CH:33]=4)[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][C:22]=4[F:24])[CH2:17][CH2:16]3)=[CH:13][C:8]=2[O:7][CH2:6]1

Participants

Conditions

Temperature: 60 °C

Procedure

The title compound is prepared from {(S)-6-[(R)-4-bromo-7-fluoro-indan-1-yloxy]-2,3-dihydro-benzofuran-3-yl}-acetic acid methyl ester (84 mg), (2-chloro-pyrid-5-yl)methylzinc chloride (0.5 moL/L in tetrahydrofuran, 1.2 mL) and tetrakis(triphenylphosphine)palladium (23 mg). Degassed tetrahydrofuran (1 mL) is added under Ar atmosphere, and the mixture is heated to 60° C. and shaken at this temperature overnight. The mixture is acidified with 4 N aqueous hydrochloric acid (1 mL) and then neutralized with saturated aqueous ammonia solution. The organic phase is separated, diluted with N,N-dimethylformamide (1 mL), and purified by HPLC on reversed phase (MeCN/water) to give the title compound. LC (method 6): tR=1.04 min.

Workup

customThe organic phase is separated
additiondiluted with N,N-dimethylformamide (1 mL)
custompurified by HPLC on reversed phase (MeCN/water)

Sources & evidence

ORD record: ord-c7b62cb8ca284d859f4101c58cfa74b6
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08809376B2

Reaction notes

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