Potassium Carbonate → HCID 85969576, compound

HRID 1916718Notes

Reaction equation

HRID 1916718 reaction equation
[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]=O)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)[C:2]#[CH:3].[NH:15]1[CH2:19][CH2:18][CH2:17][CH2:16]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C([O-])([O-])=O.[K+].[K+]>C1COCC1.C(O)(=O)C>[CH2:1]([N:4]1[C:12]2[C:7](=[CH:8][C:9]([CH2:13][N:15]3[CH2:19][CH2:18][CH2:17][CH2:16]3)=[CH:10][CH:11]=2)[CH:6]=[CH:5]1)[C:2]#[CH:3]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 31268PyrrolidineHCID 5049666Sodium triacetoxyborohydrideHCID 85969570HCID 85969570, compound

Product 1

HCID 85969576HCID 85969576, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 250 mg (1.37 mmol) 1-prop-2-ynyl-1H-indole-5-carbaldehyde and 200 μL (2.37 mmol) pyrrolidine in 50 mL THF is adjusted to pH 5 with glacial acetic acid, combined with 550 mg (2.47 mmol) NaBH(OAc)3 and stirred for 24 h at RT. 20 mL of saturated K2CO3 solution are added, the mixture is extracted with 50 mL EtOAc and the organic phase is dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5).

Workup

  1. extractionthe mixture is extracted with 50 mL EtOAc
  2. dry with materialthe organic phase is dried over Na2SO4
  3. customis purified by chromatography (silica gel, EtOAc/MeOH/NH3 95:5:0.5)

Sources & evidence

ORD record
ord-a86ddb62bc6743a6a91ed763b3103e9c
Source dataset
uspto-grants-2013_12
Patent number
US08618132B2

Reaction notes

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