Triethylamine → 7-Chloromethyl-2(naphthalene-1-sulfonyl)-7,8-dihydro-6-oxa-1,8a-diaza-acenaphthylene

HRID 33110Notes

Reaction equation

Cl[CH2:2][CH:3]([CH2:27][Cl:28])[O:4][C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][N:11]=[C:10]2[S:14]([C:17]1[C:26]2[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:20]=[CH:19][CH:18]=1)(=[O:16])=[O:15].C(N(CC)CC)C>CN(C=O)C.O>[Cl:28][CH2:27][CH:3]1[CH2:2][N:12]2[C:13]3[C:9]([C:10]([S:14]([C:17]4[C:26]5[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=5)[CH:20]=[CH:19][CH:18]=4)(=[O:15])=[O:16])=[N:11]2)=[CH:8][CH:7]=[CH:6][C:5]=3[O:4]1

Participants

Conditions

Temperature: 70 °C

Procedure

A mixture of 7-(2-chloro-1-chloromethyl-ethoxy)-3-(naphthalene-1-sulfonyl)-1H-indazole (5) (1.76 g, 4.05 mmoles) and triethylamine (0.7 ml, 4.05 mmoles) in DMF was stirred overnight at 70° C., cooled to room temperature, diluted with water and extracted with EtOAc. The extracts were combined, washed sequentially with water and brine, dried over Na2SO4 and concentrated under vacuum to afford the title compound (1.5 g, 3.85 mmoles), identified by HNMR analysis.

Workup

temperaturecooled to room temperature
extractionextracted with EtOAc
washwashed sequentially with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under vacuum

Sources & evidence

ORD record: ord-c9aaa39ae6c84be7bcc4733476d24fd9
Source dataset: uspto-grants-2008_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07429582B2

Reaction notes

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