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Triethylsilicon → tert-butyl 6-formyl-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

HRID 2001387
Notes
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Reaction equation

HRID 2001387 reaction equation
CC[SiH](CC)CC.[O:1]=[CH:2]N1S(=O)(=O)c(c2C1=O)cccc2.[CH3:3][C:4]([O:7][C:8]([N:10]1[CH2:27][c:26]([c:13]2[CH2:12][CH2:11]1)[c:17]([O:18][CH2:19][c:20]3[cH:25][cH:24][cH:23][cH:22][cH:21]3)[cH:16][c:15](Br)[cH:14]2)=[O:9])([CH3:6])[CH3:5]>>[CH3:3][C:4]([O:7][C:8]([N:10]1[CH2:27][c:26]([c:13]2[CH2:12][CH2:11]1)[c:17]([O:18][CH2:19][c:20]3[cH:25][cH:24][cH:23][cH:22][cH:21]3)[cH:16][c:15]([CH:2]=[O:1])[cH:14]2)=[O:9])([CH3:6])[CH3:5]
ParticipantsConditionsSources & evidenceReaction notes

Participants

9

Reactant 3

HCID 6327258TriethylsiliconHCID 546716891,1,3-Trioxo-1,3-dihydro-2H-1lambda~6~,2-benzothiazole-2-carbaldehydeHCID 132189892tert-butyl 6-bromo-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

Product 1

HCID 132190424tert-butyl 6-formyl-8-phenylmethoxy-3,4-dihydro-1H-isoquinoline-2-carboxylate

Reagents, catalysts & solvents 5

HCID 81531

Conditions

Temperature
80 °C

Sources & evidence

ORD record
ord-6b24817a915345fca55a08c1598f1d6e
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
Diisopropylethylamine
Reagent
HCID 167845palladium(II) acetateCatalyst
HCID 534858451-[3,5-Bis(trifluoromethyl)phenyl]-3,4-bis(2R,5R)(2,5-dimethylphospholan-1-yl)-1H-pyrrole-2,5-dioneCatalyst
HCID 6228DimethylformamideSolvent
HCID 117669-PhenylanthraceneInternal standard