Triethylamine → HCID 117778783, compound

HRID 1526997Notes

Reaction equation

HRID 1526997 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 4 A 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-29ceac6ea8244dbea427e5af28c0db70
Source dataset
uspto-grants-2015_07
Patent number
US09085583B2

Reaction notes

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