Ethyl 4-bromobutyrate → HCID 53888556, compound

HRID 1733925Notes

Reaction equation

[O:1]=[C:2]1[CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.Br[CH2:25][CH2:26][CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]>>[CH2:31]([O:30][C:28](=[O:29])[CH2:27][CH2:26][CH2:25][C:10]1([CH2:11][C:12]2[CH:17]=[CH:16][N:15]=[CH:14][N:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]([C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)[C:2]1=[O:1])[CH3:32]

Participants

Reactant 2

HCID 76300Ethyl 4-bromobutyrate

HCID 194389562,3-Dihydro-2-oxo-1-phenyl-3-(4-pyrimidinylmethyl)1H-indole

Product 1

HCID 53888556HCID 53888556, compoundYield 55%

Procedure

By substituting 2,3-dihydro-2-oxo-1-phenyl-3-(4-pyrimidinylmethyl)-1H-indole and ethyl 4-bromobutyrate in Example 1, the desired product was obtained in 55% yield as an oil; NMR(CDCl3TMS) δ1.22 (t, 3H, J=7 Hz); 1.42 (m, 1H); 1.53 (m, 1H); 2.06 (m, 1H); 2.25 (m, 3H); 3.25 (d, 1H, J=14 Hz); 3.55 (d, 1H, J=14 Hz); 4.09 (q, 2H, J=7 Hz); 6.63 (d, 1H, J=8 Hz); 6.98 (m, 1H); 7.07 (m, 2H); 7.26 (m, 3H); 7.40 (m, 1H); 7.50 (m, 2H); 8.42 (d, 1H, J=5 Hz); 8.90 (s, 1H). IR(KBr): 1728, 1583, 1501, 1481, 1466, 1376, 1326, 1182, 1157, 758, 700 cm-1 ; mass spec m/e 416 (M+1); high resolution mass spec m/e calcd 416.197417, m/e found 416.196591 (M+H).

Sources & evidence

ORD record: ord-ef4eabc6f2564b078c501b8cfea04569
Source dataset: uspto-grants-1996_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05532247

Reaction notes

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