Triethylamine → 5-Cyano-3-methyl-2-pyridin-3-yl-indole-1-carboxylic acid tert-butyl ester
Reaction equation
[CH3:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]#[N:12])[CH:9]=2)[NH:4][C:3]=1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1.C(N(CC)CC)C.[C:26](=O)([O:32]C(C)(C)C)[O:27][C:28]([CH3:31])([CH3:30])[CH3:29]>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:28]([O:27][C:26]([N:4]1[C:5]2[C:10](=[CH:9][C:8]([C:11]#[N:12])=[CH:7][CH:6]=2)[C:2]([CH3:1])=[C:3]1[C:13]1[CH:14]=[N:15][CH:16]=[CH:17][CH:18]=1)=[O:32])([CH3:31])([CH3:30])[CH3:29]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of 3-methyl-2-pyridin-3-yl-1H-indole-5-carbonitrile (Example 6, 96 mg, 0.40 mmol) in DMF (2 mL) at room temperature is added triethylamine (30 mg, 0.30 mmol), di-tert-butyl carbonate (65 mg, 0.30 mmol) and 4-(N,N-dimethylamino)pyridine (2 mg, 0.020 mmol). The mixture is stirred under N2. The mixture is purified by Xbridge RP18 with a gradient of acetonitrile in 0.1% aqueous ammonium hydroxide to give 5-cyano-3-methyl-2-pyridin-3-yl-indole-1-carboxylic acid tert-butyl ester as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 1.30 (s, 9H), 2.16 (s, 3H), 7.47-7.55 (m, 1H), 7.65 (dd, J=8.7, 1.6 Hz, 1H), 7.76 (d, J=7.3 Hz, 1H), 7.90 (d, J=1.0 Hz, 1H), 8.35 (d, J=8.6 Hz, 1H), 8.63 (d, J=1.8 Hz, 1H), 8.69 (dd, J=5.1, 1.5 Hz, 1H). HRMS (ESI) m/z 334.1566 [(M+H)+ Calcd for C20H20N3O2: 334.1556].
Workup
- customThe mixture is purified by Xbridge RP18 with a gradient of acetonitrile in 0.1% aqueous ammonium hydroxide
Sources & evidence
- ORD record
- ord-3ad458ae68004b84bb028e4448a4abe1
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242963B2
Reaction notes
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