p-Xylyl bromide → HCID 88172433, compound

HRID 2304757Notes

Reaction equation

HRID 2304757 reaction equation
[C:1]1([CH2:7][O:8][C:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[NH:11][C:10]=2C(OC)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1.[N:33]1[CH:38]=[CH:37][CH:36]=[C:35]([NH-:39])[CH:34]=1.[Li+].C1C[O:44][CH2:43]C1>>[CH3:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][N:11]2[C:12]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[C:9]([O:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:10]2[N:39]([C:35]2[CH:34]=[N:33][CH:38]=[CH:37][CH:36]=2)[CH:43]=[O:44])=[CH:27][CH:26]=1

Participants

6

Reactant 5

HCID 7721p-Xylyl bromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 18435811HCID 18435811, compoundHCID 23711720HCID 23711720, compound

Product 1

HCID 88172433HCID 88172433, compound

Procedure

Following the procedure describing the preparation of example 6, methyl 3-(phenylmethoxy)indole-2-carboxylate (100 mg) in DMP (5.0 mL) was treated with 12 mg of a NaH suspension (60% in oil) followed by 4-methybenzyl bromide (100 mL). After work-up the crude alkylated material was taken up in dry THF (10 mL) and treated with the lithium 3-pyridylamide (0.3 M in THF) solution as describied previously. Following work-up and purification by flash chromatography the title indole (58.7 mg) was obtained as a white solid.

Workup

  1. customwork-up and purification by flash chromatography the title indole (58.7 mg)
  2. customwas obtained as a white solid

Sources & evidence

ORD record
ord-94d2de7ac7c34b69a1bef73dd9e095a8
Source dataset
uspto-grants-2002_08
Patent number
US06436965B1

Reaction notes

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