Acetonitrile → HCID 89657458, compound

HRID 1775245Notes

Reaction equation

HRID 1775245 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[C:5]2[CH:6]=[C:7]([C@@:11]3([CH3:16])[CH2:15][CH2:14][CH2:13][NH:12]3)[NH:8][C:9]=2[CH:10]=1.CC#N.[CH3:24][O:25][C:26](=[O:29])[CH2:27]Br.CCN(C(C)C)C(C)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([C:17]([O:19][CH3:20])=[O:18])[C:5]2[CH:6]=[C:7]([C@@:11]3([CH3:16])[CH2:15][CH2:14][CH2:13][N:12]3[CH2:27][C:26]([O:25][CH3:24])=[O:29])[NH:8][C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 89657176HCID 89657176, compound

Product 1

HCID 89657458HCID 89657458, compoundYield 63.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred mixture of (R)-methyl 6-fluoro-2-(2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate (1.0, 1.27 mol), CH3CN (50 ml) and methylbromoacetate (0.58 g, 3.82 mmol) was added DIPEA (0.82 g, 6.35 mmol). The reaction mixture was stirred at room temperature for about 20 hours. The reaction mixture was then diluted with CH2Cl2 (15 ml) and washed with water three times. The organic layer was dried with MgSO4 and concentrated to give 0.85 g of (R)-methyl 6-fluoro-2-(1-(2-methoxy-2-oxoethyl)-2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate. 1H NMR (CD3OD-d4) δ 7.47 (dd, 1H, J=2.4, 12.0 Hz), 7.27 (dd, 1H, J=2.4, 9.0 Hz), 6.89 (s, 1H), 3.95 (s, 3H), 3.66-3.68 (m, 1H), 3.64 (s, 3H), 3.16-3.17 (m, 2H), 2.72-2.75 (m, 1H), 1.88-2.02 (m, 4H), and 1.44 (s, 3H). MS (ESI) m/e [M+1]+ 349.0.

Workup

  1. washwashed with water three times
  2. dry with materialThe organic layer was dried with MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-cc844b0ff56a434ba9426c825a80621b
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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