Water → HCID 22462783, compound

HRID 1937184Notes

Reaction equation

C([O:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:20][CH:19]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([OH:38])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:39]=1)C1C=CC=CC=1.Br[CH2:41][CH2:42][CH2:43][C:44]#[N:45].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[OH:8][C:9]1[CH:10]=[CH:11][C:12]2[C:16]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([O:24][CH2:25][CH2:26][N:27]4[CH2:31][CH2:30][CH2:29][CH2:28]4)=[CH:22][CH:23]=3)=[C:15]([C:32]3[CH:37]=[CH:36][C:35]([O:38][CH2:41][CH2:42][CH2:43][C:44]#[N:45])=[CH:34][CH:33]=3)[S:14][C:13]=2[CH:39]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 6-benzyloxy-2-(4-hydroxyphenyl)-3-[4-[2-(1-pyrrolidinyl)ethoxy]benzyl]benzo[b]thiophene (Part D), 4-bromobutyronitrile (1.2 mol/mol of phenol), and Cs2CO3 (2 mol/mol of phenol) in DMF (about 10 mL/mmol of phenol) was heated to 80° C. for 3 h, poured into 4 volumes of water and extracted with EtOAc. After drying (K2CO3) and evaporation, the title compound was obtained as a foam in 98% yield following MPLC (SiO2; 0.5% in CHCl3 sat'd with NH4OH).

Workup

extractionextracted with EtOAc
customAfter drying
custom(K2CO3) and evaporation

Sources & evidence

ORD record: ord-0e93456421824f3fbf10993a2e155509
Source dataset: uspto-grants-2002_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06391901B1

Reaction notes

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