Sodium hydride → HCID 15292754, compound

HRID 2210601Notes

Reaction equation

HRID 2210601 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([O:26][CH2:27][C:28]6[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=6)=[CH:23][CH:24]=5)[NH:19][CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1.[H-].[Na+].Cl[C:37]([O:39][C:40]1[CH:45]=[CH:44][C:43]([N+:46]([O-:48])=[O:47])=[CH:42][CH:41]=1)=[O:38]>CN(C=O)C>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:15]([C:17]4[C:25]5[C:20](=[CH:21][C:22]([O:26][CH2:27][C:28]6[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=6)=[CH:23][CH:24]=5)[N:19]([C:37]([O:39][C:40]5[CH:41]=[CH:42][C:43]([N+:46]([O-:48])=[O:47])=[CH:44][CH:45]=5)=[O:38])[CH:18]=4)=[O:16])=[C:10]3[CH2:9][S:8]2)[CH:2]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 821294-Nitrophenyl chloroformateHCID 15292729HCID 15292729, compound

Product 1

HCID 15292754HCID 15292754, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-(pyridin-3-yl)-7-(6-phenylmethoxyindol-3-yl)carbonyl-1H,3H-pyrrolo[1,2-c]thiazole (200 mg, 0.443 mmol), prepared as in Example 4, in DMF (12 mL) was added NaH (60% oil dispersion, 19 mg, 0.465 mmol) and the reaction mixture was stirred for 7 min at ambient temperature. 4-nitrophenyl chloroformate (94 mg, 0.45 mmol) was added and the amber solution was stirred for two hours at ambient temperature. The reaction mixture was partitioned between H2O and ethyl acetate. The organic phase was dried over MgSO4, filtered,and concentrated. The title compound (98 mg), was purified by flash chromatography on silica gel (60 g, 1:1 ethyl acetate, hexanes).

Workup

  1. stirringthe amber solution was stirred for two hours at ambient temperature
  2. customThe reaction mixture was partitioned between H2O and ethyl acetate
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationfiltered,and concentrated
  5. customThe title compound (98 mg), was purified by flash chromatography on silica gel (60 g, 1:1 ethyl acetate, hexanes)

Sources & evidence

ORD record
ord-f4ed8687ec0b46dd838cf309da29880c
Source dataset
uspto-grants-1995_10
Patent number
US05459152

Reaction notes

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