Triethylamine → HCID 117778783, compound

HRID 2206627Notes

Reaction equation

HRID 2206627 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2.[C:15]1(B(O)O)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C([Cu]C(=O)C)(=O)C.C(N(CC)CC)C>CN(C)C1C=CN=CC=1.ClCCl>[CH3:1][C:2]1[N:3]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[C:4]2[C:9]([C:10]=1[C:11]([O:13][CH3:14])=[O:12])=[CH:8][CH:7]=[CH:6][CH:5]=2

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 594174Methyl 2-methyl-1H-indole-3-carboxylateHCID 178473700HCID 178473700, compound

Product 1

HCID 117778783HCID 117778783, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 2-methyl-1H-indole-3-carboxylate (500 mg, 2.65 mmol), phenylboronic acid (384 mg, 3.17 mmol), diacetylcopper (453 mg, 3.98 mmol), triethylamine (0.44 ml, 3.98 mmol), N,N-dimethylpyridin-4-amine (486 ml, 3.98 mmol) and 4A molecular sieve (1.02 g) in dichloromethane (15 mL) was stirred at room temperature for 12 hours. After filtration, the mixture was concentrated and purified by chromatography (silica gel, petroleum: ethyl acetate=10:1) to afford methyl 2-methyl-1-phenyl-1H-indole-3-carboxylate as white solid (272 mg, 39%). 1H NMR (400 MHz, CDCl3) δ 8.19 (d, J=8.0 Hz, 1H), 7.66-7.51 (m, 3H), 7.36 (dd, J=5.3, 3.2 Hz, 2H), 7.30 (s, 1H), 7.21-7.14 (m, 1H), 7.04 (d, J=8.2 Hz, 1H), 4.00 (s, 3H), 2.62 (s, 3H).

Workup

  1. filtrationAfter filtration
  2. concentrationthe mixture was concentrated
  3. custompurified by chromatography (silica gel, petroleum: ethyl acetate=10:1)

Sources & evidence

ORD record
ord-421f24003cb04881a3e8f8edef479566
Source dataset
uspto-grants-2016_06
Patent number
US09371331B2

Reaction notes

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