Tetrahydrofuran → 7-Chloro-3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridine

HRID 590836Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)[C:5]2[C:20](I)=[N:21][N:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:4]=2[CH:3]=1.CC([O-])(C)C.[Na+].C1COCC1>CC(OC1C=CC=C(OC(C)C)C=1C1C(P(C2CCCCC2)C2CCCCC2)=CC=CC=1)C.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:22]([C:23]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)([C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:21]=[C:20]3[C:5]2=[C:6]([CH2:8][CH2:9][N:10]3[CH2:11][C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)[N:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)-N-(4-methoxybenzyl)ethanamine (268 mg, 0.391 mmol) and RuPhos pre-catalyst (16 mg, 0.02 mmol) were charged in a 1 dram vial, evacuated and backfilled with nitrogen and taken in 1,4-dioxane (2 mL). Added a solution of 2M NaOtBu in THF (0.5 ml, 0.978 mmol) and reaction heated to 55° C. for 1 hour. The reaction mixture was diluted with EtOAc and washed with water, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-25% EtOAc-hexanes) gave 7-chloro-3-(4-methoxybenzyl)-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridine. MS ESI calc'd. for C35H29 ClN4O [M+H]+ 558. found 558.

Workup

customevacuated
additionAdded
washwashed with water, brine
dry with materialdried with sodium sulfate
concentrationconcentrated
customPurification of the residue by flash column (0-25% EtOAc-hexanes)

Sources & evidence

ORD record: ord-a7634afc46984096a5da1a22a717af61
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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