4-Benzyloxy-2(1H)-pyridone → HCID 57950402, compound

HRID 930790Notes

Reaction equation

Br[C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:19][CH2:18][C:7]=3[N:8](C(OC(C)(C)C)=O)[C:9]=2[CH:10]=1.[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][NH:40][C:39](=[O:43])[CH:38]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>>[CH2:29]([O:36][C:37]1[CH:42]=[CH:41][N:40]([C:2]2[CH:3]=[CH:4][C:5]3[C:6]4[CH2:21][N:20]([C:22]([O:24][C:25]([CH3:27])([CH3:28])[CH3:26])=[O:23])[CH2:19][CH2:18][C:7]=4[NH:8][C:9]=3[CH:10]=2)[C:39](=[O:43])[CH:38]=1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

Reactant 2

HCID 36077244-Benzyloxy-2(1H)-pyridone

HCID 57950349HCID 57950349, compound

Product 1

HCID 57950402HCID 57950402, compoundYield 12.1%

Procedure

Prepared from di-tert-butyl 7-bromo-3,4-dihydro-1H-pyrido[4,3-b]indole-2,5-dicarboxylate (1.24 g, 2.72 mmol) and 4-benzyloxypyridone (547 mg, 2.72 mmol) according to the procedure of Example 1 (step c). Purification by flash column chromatography (silica gel, hexanes/ethyl acetate, 100:0 to 80:20 to 50:50 to 25:75 then 0:100) gave the title compound (155 mg, 10%) as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.40 (br s, 1H), 7.44-7.38 (m, 5H), 7.30 (d, J=7.5 Hz, 1H), 7.22 (d, J=8.2 Hz, 1H), 7.16 (s, 1H), 6.82 (dd, J=8.2, 1.4 Hz, 1H), 6.12-6.09 (m, 2H), 5.09 (s, 2H), 4.46 (br s, 2H), 3.70 (br m, 2H), 2.54 (br m, 2H), 1.50 (s, 9H).

Workup

customPurification by flash column chromatography (silica gel, hexanes/ethyl acetate, 100:0 to 80:20 to 50:50 to 25:75

Sources & evidence

ORD record: ord-6515095e51e048bfade62b727425c45c
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296743B2

Reaction notes

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