Acetic Acid → HCID 86618255, compound

HRID 1159816Notes

Reaction equation

HRID 1159816 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]2[N:8]([S:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:7]=[CH:6][C:5]=2[C:4]=1[CH:21]=O.[C:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.ClCCl.C([O-])([O-])=O.[Na+].[Na+]>[CH3:1][O:2][C:3]1[C:4]([CH2:21][N:33]2[CH2:32][CH2:31][N:30]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:35][CH2:34]2)=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([S:12]([C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH:7]=[CH:6]2

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 143452tert-Butyl piperazine-1-carboxylateHCID 5049666Sodium triacetoxyborohydrideHCID 86618256HCID 86618256, compound2×

Product 1

HCID 86618255HCID 86618255, compound

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 10340Sodium CarbonateSolvent

Procedure

5-Methoxy-1-(phenylsulfonyl)-1H-indole-4-carbaldehyde (0.10 g, 0.317 mmol, Intermediate 75), boc-piperazine (0.118 g, 0.634 mmol) and acetic acid (0.095 g, 1.58 mmol) were dissolved in THF (5 mL) and sodium triacetoxyborohydride (0.134 g, 0.63 mmol) were added. The mixture was stirred for 2 hours and diluted with dichloromethane and 1N Na2CO3. The mixture was extracted with dichloromethane (2×) and the combined organics were dried (MgSO4) and evaporated. The crude product was ran through a plug of silica gel eluating with 5% MeOH in dichloromethane. Yield 100 mg (65%). White solid.

Workup

  1. extractionThe mixture was extracted with dichloromethane (2×)
  2. dry with materialthe combined organics were dried (MgSO4)
  3. customevaporated

Sources & evidence

ORD record
ord-41ac0b4d83bb4b37a21d5478e84ec1ec
Source dataset
uspto-grants-2010_10
Patent number
US07812017B2

Reaction notes

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