HCID 69281970, compound → HCID 87765531, compound

HRID 2362393Notes

Reaction equation

HRID 2362393 reaction equation
Br[C:2]1[CH:3]=[C:4]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C@@H:9]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])[OH:10])C=NC=1.[Br:27][C:28]1[N:33]=C(/C=C/C2C=C(F)C=CC=2F)C=C[N:29]=1>>[Br:27][C:28]1[N:33]=[C:4]([C@@H:8]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:23])([CH3:24])[CH3:25])[C@@H:9]([C:11]2[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:12]=2[F:18])[OH:10])[CH:3]=[CH:2][N:29]=1

Participants

3

Reactant 2

HCID 69281970HCID 69281970, compoundHCID 86673429HCID 86673429, compound

Product 1

HCID 87765531HCID 87765531, compound

Procedure

Prepared according to the same procedure as tert-butyl (1R,2R)-1-(5-bromopyridin-3-yl)-2-(2,5-difluorophenyl)-2-hydroxyethylcarbamate, starting with (E)-2-bromo-4-(2,5-difluorostyryl)pyrimidine. 1H NMR (500 MHz, DMSO-d6) δ 8.70 (d, J=5.2 Hz, 1H), 7.65 (d, J=5.2 Hz, 1H), 7.45 (d, J=9.8 Hz, 1H), 7.29 (ddd, J=9.0, 5.3, 3.4 Hz, 1H), 7.22-7.10 (m, 2H), 5.82 (d, J=5.2 Hz, 1H), 5.46-5.30 (m, 1H), 4.85 (dd, J=9.8, 3.1 Hz, 1H), 1.29-1.03 (m, 9H), Mass spec.: 432.1 (MH)+.

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-b801943392db49929279c80f268e4a9e
Source dataset
uspto-grants-2014_04
Patent number
US08691821B2

Reaction notes

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