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

HRID 2002066Notes

Reaction equation

HRID 2002066 reaction equation
CC[SiH](CC)CC.C[Si](c1ccccc1)(c2ccccc2)[C:1](O)=[O:2].[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:1]=[O:2])[cH:14]2)=[O:9])([CH3:6])[CH3:5]

Participants

9

Reactant 3

HCID 6327258TriethylsiliconHCID 679740191-Methyl-1,1-diphenylsilanecarboxylic acidHCID 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 81531DiisopropylethylamineReagentHCID 448383(3R,4R,5R,6R)-5-acetamido-2-[[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-3-fluoro-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acidReagentHCID 75537289[1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichlormethaneCatalystHCID 6228DimethylformamideSolventHCID 117669-PhenylanthraceneInternal standard

Conditions

Temperature
90 °C

Sources & evidence

ORD record
ord-4557e1e5c3c3470ea750a8b7866f53e0
Source dataset
39k HTE dataset from Pfizer
Original link
View source

Reaction notes

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