Sodium Carbonate → HCID 44467946, compound

HRID 1642459Notes

Reaction equation

HRID 1642459 reaction equation
I[C:2]1[C:7](=[O:8])[N:6]2[C:9]([C:12]([F:15])([F:14])[F:13])=[CH:10][S:11][C:5]2=[N:4][C:3]=1/[CH:16]=[CH:17]/[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH3:25])[C:19]=1[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29].[C:32]([C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)#[N:33].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.C(O)C.O>[CH3:25][O:24][C:20]1[C:19]([O:26][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[C:18](/[CH:17]=[CH:16]/[C:3]2[N:4]=[C:5]3[S:11][CH:10]=[C:9]([C:12]([F:15])([F:14])[F:13])[N:6]3[C:7](=[O:8])[C:2]=2[C:37]2[CH:38]=[CH:39][C:34]([C:32]#[N:33])=[CH:35][CH:36]=2)[CH:23]=[CH:22][CH:21]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 27343264-Cyanophenylboronic acidHCID 86636082HCID 86636082, compound

Product 1

HCID 44467946HCID 44467946, compoundYield 65.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

This compound was prepared from Intermediate 21 (100 mg, 0.197 mmol) and 4-cyanophenylboronic acid (35 mg, 0.204 mmol) using Pd[(C6H5)3P]4 (8 mg, 0.007 mmol) and sodium carbonate (112 mg, 1.053 mmol) in toluene (10 ml) and ethanol (5 ml) and water (4 ml) according to the procedure outlined in Example 1 to afford crude residue which was purified by column chromatography using 1% ethyl acetate in chloroform to afford 70 mg of the desired product; 1H NMR (300 MHz, DMSO-d6) δ 1.03 (s, 9H), 3.53 (m, 2H), 3.77 (m, 2H), 6.72-6.77 (m, 1H), 6.98-7.02 (m, 2H), 7.52-7.55 (m, 2H), 7.91-7.94 (m, 2H), 8.24 (s, 1H), 8.30 (s, 2H); ESI-MS (m/z) 540.53 (M+H)+.

Workup

  1. customto afford crude residue which
  2. customwas purified by column chromatography

Sources & evidence

ORD record
ord-4f20be7ae1664feca90f799c70374bec
Source dataset
uspto-grants-2012_02
Patent number
US08119647B2

Reaction notes

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