Iodoacetamide → HCID 69663879, compound

HRID 1246939Notes

Reaction equation

HRID 1246939 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][NH:9]2)=[CH:5][CH:4]=1.[H-].[Na+].I[CH2:15][C:16]([NH2:18])=[O:17]>CN(C=O)C>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([CH:7]=[CH:8][N:9]2[CH2:15][C:16]([NH2:18])=[O:17])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 3727IodoacetamideHCID 24758Sodium hydrideHCID 766596-Methoxy-1H-indole

Product 1

HCID 69663879HCID 69663879, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Intermediate C12 was prepared as described for Intermediate C2 using 6-methoxyindole (489 mg, 3.32 mmol), sodium hydride (160 mg, 3.98 mmol) and iodoacetamide (615 mg, 3.32 mmol) in DMF (50 mL). Two recrystallizations from ethyl acatete yielded intermediate C12 as a whte solid (252 mg, 37%). m.p. 210.1–211.0° C. 1H NMR (200 MHz, DMSO-D6) δ 7.48 (br s, 1H), 7.41 (d, 8.6 Hz, 1H), 7.25 (br s, 1H), 7.16 (d, 3.2 Hz, 1H), 6.91 (d, 2.0 Hz, 1H), 6.69 (dd, 6.4 Hz, 2.2 Hz, 1H), 6.35 (d, 0.8 Hz, 1H), 4.74 (s, 2H), 3.77 (s, 3H).

Workup

  1. customIntermediate C12 was prepared
  2. customTwo recrystallizations from ethyl acatete yielded intermediate C12 as a whte solid (252 mg, 37%)

Sources & evidence

ORD record
ord-46aaffc5b90f42a7aec06964c8d62868
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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