Methyl bromoacetate → HCID 89657509, compound

HRID 1775241Notes

Reaction equation

HRID 1775241 reaction equation
[CH3:1][C@:2]1([C:7]2[NH:8][C:9]3[CH:10]=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[C:14]=3[CH:15]=2)[CH2:6][CH2:5][CH2:4][NH:3]1.[CH3:20][O:21][C:22](=[O:25])[CH2:23]Br.CCN(C(C)C)C(C)C>CC#N.C(Cl)Cl>[CH3:20][O:21][C:22](=[O:25])[CH2:23][N:3]1[CH2:4][CH2:5][CH2:6][C@@:2]1([C:7]1[NH:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]([C:16]([O:18][CH3:19])=[O:17])[C:14]=2[CH:15]=1)[CH3:1]

Participants

6

Reactant 3

HCID 60984Methyl bromoacetateHCID 81531DiisopropylethylamineHCID 89657501HCID 89657501, compound

Product 1

HCID 89657509HCID 89657509, compoundYield 59.7%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6344DichloromethaneSolvent

Procedure

(R)-Methyl 2-(2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate (190 mg, 0.74 mmol) was dissolved in CH3CN (25 ml) and methylbromoacetate (250 mg, 1.6 mmol). DIPEA (350 mg, 2.7 mmol) was then added. 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 146 mg of (R)-methyl 2-(1-(2-methoxy-2-oxoethyl)-2-methylpyrrolidin-2-yl)-1H-indole-4-carboxylate. 1H NMR (CDCl3-d) δ 7.85 (d, 1H, J=7.8 Hz), 7.13-7.29 (m, 3H), 4.92 (s, 2H), 3.95 (s, 3H), 3.70 (s, 3H), 3.56-3.62 (m, 2H), 1.95-2.06 (m, 4H), and 1.94 (s, 3H). MS (ESI) m/e [M+1]+ 331.0.

Workup

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

Sources & evidence

ORD record
ord-61f6553e85da43f794b6df519f7d6192
Source dataset
uspto-grants-2016_02
Patent number
US09260440B2

Reaction notes

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