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

HRID 590847Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][CH2:9][NH:10][CH2:11][CH3:12])[C:5]2[C:13](I)=[N:14][N:15]([C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=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:15]([C:16]([C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[N:14]=[C:13]3[C:5]2=[C:6]([CH2:8][CH2:9][N:10]3[CH2:11][CH3:12])[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-ethylethanamine (160 mg, 0.270 mmol) and RuPhos pre-catalyst (19.6 mg, 0.027 mmol) were charged in a 1 dram vial, evacuated and backfilled with nitrogen and taken in toluene (1.8 mL) before a solution of 2M NaOtBu in THF (0.34 ml, 0.675 mmol) was added. 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-ethyl-1-trityl-1,3,4,5-tetrahydropyrazolo[3,4,5-de][1,6]naphthyridine. MS ESI calc'd. for C29H25ClN4 [M+H]+ 465. found 465.

Workup

customevacuated
additionwas added
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-3ecc895f83124e1f8fff63f7aa8a6a3f
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09233979B2

Reaction notes

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