Tetrahydrofuran → HCID 118272360, compound

HRID 590850Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][NH:10][CH:11]([CH3:13])[CH3:12])[C:5]2[C:14](I)=[N:15][N:16]([C:17]([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:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=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.C1(C)C=CC=CC=1.CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[N:16]([C:17]([C:24]3[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=3)([C:18]3[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[N:15]=[C:14]3[C:5]2=[C:6]([CH2:8][CH2:9][N:10]3[CH:11]([CH3:12])[CH3:13])[N:7]=1

Participants

Conditions

Temperature: 55 °C

Procedure

N-(2-(6-chloro-3-iodo-1-trityl-1H-pyrazolo[4,3-c]pyridin-4-yl)ethyl)propan-2-amine (554 mg, 0.913 mmol) and RuPhos pre-catalyst (66.5 mg, 0.091 mmol) were charged in a 2 dram vial, evacuated and backfilled with nitrogen and taken in toluene (4 mL) before the addition of a solution of 2M NaOtBu in THF (1.15 mL, 2.3 mmol). The reaction mixture was heated at 55° C. for 1 hour before it was diluted with EtOAc and washed with water, brine, dried with sodium sulfate and concentrated. Purification of the residue by flash column (0-50% EtOAc-hexanes) gave 7-chloro-3-isopropyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridine. MS ESI calc'd. for C30H27ClN4 [M+H]+ 480. found 480.

Workup

customevacuated
washwashed with water, brine
dry with materialdried with sodium sulfate
concentrationconcentrated
customPurification of the residue by flash column (0-50% EtOAc-hexanes)

Sources & evidence

ORD record: ord-f97dcd0be41c466eb64a72203279052d
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

Loading…