Sodium hydride → HCID 67595562, compound

HRID 1417970Notes

Reaction equation

[H-].[Na+].[CH3:3][CH:4]([O:6][C:7]([C:9]1[N:29]=[CH:28][C:12]2[NH:13][C:14]3[C:19]([C:11]=2[C:10]=1[CH2:30][O:31][CH3:32])=[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]=[CH:16][CH:15]=3)=[O:8])[CH3:5].[CH3:33][O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46]Br)=[CH:37][CH:36]=1>O1CCCC1>[CH3:5][CH:4]([O:6][C:7]([C:9]1[N:29]=[CH:28][C:12]2[N:13]([CH2:46][CH2:45][CH2:44][CH2:43][CH2:42][CH2:41][C:38]3[CH:37]=[CH:36][C:35]([O:34][CH3:33])=[CH:40][CH:39]=3)[C:14]3[C:19]([C:11]=2[C:10]=1[CH2:30][O:31][CH3:32])=[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:17]=[CH:16][CH:15]=3)=[O:8])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

10 mg of an 80% suspension of sodium hydride in oil is mixed with 10 ml of tetrahydrofuran and to 0° C. 404.5 mg of 5-benzyloxy-4-methoxymethyl-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is added to the suspension, it is stirred for 10 minutes at 0° C., mixed with 406 mg of 6-(4-methoxyphenyl)-hexyl bromide, and the reaction mixture is stirred for 16 hours at room temperature. After the reaction mixture is worked up as described, 330 mg of 5-benzyloxy-4-methoxymethyl-9-[6-(4-methoxyphenyl)-hexyl]-9H-pyrido[3,4-b]indole-3-carboxylic acid-(1-methylethyl)-ester is obtained.

Workup

stirringthe reaction mixture is stirred for 16 hours at room temperature

Sources & evidence

ORD record: ord-e8861342bc314422b24c718bbbb0fb21
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05880126

Reaction notes

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