HCID 57561730, compound → HCID 59153332, compound

HRID 601938Notes

Reaction equation

HRID 601938 reaction equation
O=[C:2]1[CH2:10][CH2:9][CH2:8][C:7]2[N:6]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:5]([C:19]([O:21][CH3:22])=[O:20])=[CH:4][C:3]1=2.[CH2:23]([Mg]Cl)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[CH:23](=[C:2]1/[C:3]2[CH:4]=[C:5]([C:19]([O:21][CH3:22])=[O:20])[N:6]([CH2:11][O:12][CH2:13][CH2:14][Si:15]([CH3:18])([CH3:17])[CH3:16])[C:7]=2[CH2:8][CH2:9][CH2:10]/1)\[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

3

Reactant 2

HCID 57561730HCID 57561730, compoundHCID 178418336HCID 178418336, compound2×

Product 1

HCID 59153332HCID 59153332, compound

Procedure

The title compound was synthesized from methyl 4-oxo-1-((2-(trimethylsilyl)ethoxy)methyl)-4,5,6,7-tetrahydro-1H-indole-2-carboxylate (900 mg, 2.78 mmol) and benzylmagnesium chloride (3.4 mL, 2M in THF, 6.8 mmol) according to General Procedure 3. In this example, additional benzylmagnesium chloride (1.7 mL, 2M in THF, 3.4 mmol) was added after 2 h. The crude product (900 mg) was used in the next step without further purification. LC/MS: 50%, m/z=397.

Workup

  1. customwas added after 2 h
  2. customThe crude product (900 mg) was used in the next step without further purification

Sources & evidence

ORD record
ord-9db0426fcf53446b889858e0129d096e
Source dataset
uspto-grants-2011_03
Patent number
US07902252B2

Reaction notes

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