2-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → 9-tert-butyl-2-(3-pyridyl)-14-(3,6-dihydro-2H-thiopyran-4-yl)-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HRID 1971757Notes

Reaction equation

[C:1]([N:5]1[CH2:37][CH2:36][CH2:35][CH2:34][C:8]2[C:9]([C:28]3[CH2:29][CH2:30]O[CH2:32][CH:33]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[C:16]([O:26][CH3:27])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:38])([CH3:4])([CH3:3])[CH3:2].C(N1CCCCC2C(Br)=C3C4C=C(C5C=NC=CC=5)C(OC)=CC=4CCN3C=2C1=O)(C)(C)C.[S:72]1CC=C(B2OC(C)(C)C(C)(C)O2)CC1>>[C:1]([N:5]1[CH2:37][CH2:36][CH2:35][CH2:34][C:8]2[C:9]([C:28]3[CH2:29][CH2:30][S:72][CH2:32][CH:33]=3)=[C:10]3[C:19]4[CH:18]=[C:17]([C:20]5[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=5)[C:16]([O:26][CH3:27])=[CH:15][C:14]=4[CH2:13][CH2:12][N:11]3[C:7]=2[C:6]1=[O:38])([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 467397352-(3,6-Dihydro-2H-thiopyran-4-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane

HCID 581248489-tert-butyl-2-(3-pyridyl)-14-bromo-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

HCID 581249569-tert-butyl-2-(3-pyridyl)-14-(3,6-dihydro-2H-pyran-4-yl)-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Product 1

HCID 509061419-tert-butyl-2-(3-pyridyl)-14-(3,6-dihydro-2H-thiopyran-4-yl)-3-methoxy-5,6,10,11,12,13-hexahydroazocino[4',3':4,5]pyrrolo[2,1-a]isoquinolin-8(9H)-one

Procedure

Compound 25d was synthesized in a similar way as 25c, starting from 40 mg 25b and 21.4 mg 2-(3,6-dihydro-2H-thiopyran-4-yl)-4,4,5,5,-tetramethyl-1,3,2-dioxaborolane to give 1.4 mg of compound 25d.

Sources & evidence

ORD record: ord-9cbc14f53fa949e591e4037a6ee08099
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431564B2

Reaction notes

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