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(Difluoromethyl)trimethylsilane → tert-butyl 6-(difluoromethyl)-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

HRID 2033438
Notes
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Reaction equation

HRID 2033438 reaction equation
[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:25][c:24]([c:11]2[CH2:10][CH2:9]1)[c:15]([O:16][CH2:17][c:18]3[cH:23][cH:22][cH:21][cH:20][cH:19]3)[cH:14][c:13](Br)[cH:12]2)=[O:7])([CH3:4])[CH3:3].C[Si]([CH:26]([F:28])[F:27])(C)C>>[CH3:1][C:2]([O:5][C:6]([N:8]1[CH2:25][c:24]([c:11]2[CH2:10][CH2:9]1)[c:15]([O:16][CH2:17][c:18]3[cH:23][cH:22][cH:21][cH:20][cH:19]3)[cH:14][c:13]([CH:26]([F:28])[F:27])[cH:12]2)=[O:7])([CH3:4])[CH3:3]
ParticipantsConditionsSources & evidenceReaction notes

Participants

8

Reactant 2

HCID 11170968(Difluoromethyl)trimethylsilaneHCID 132189892tert-butyl 6-bromo-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

Product 1

HCID 132190055tert-butyl 6-(difluoromethyl)-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

Reagents, catalysts & solvents 5

HCID 23676156Sodium t-butoxideReagentHCID 634876

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-5d323425c71047199662e9b5546b7275
Source dataset
39k HTE dataset from Pfizer
DOI
10.1038/s41557
Original link
View source

Reaction notes

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On this pageParticipantsConditionsSources & evidenceReaction notes
Binap, (A+-)-
Catalyst
HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumCatalyst
HCID 312751,4-DioxaneSolvent
HCID 117669-PhenylanthraceneInternal standard