tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylate → Biphenyl

HRID 608167Notes

Reaction equation

HRID 608167 reaction equation
CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(Cl)c(C)cc21.CC1(C)OB(c2cn(S(=O)(=O)c3ccccc3)c3ncccc23)OC1(C)C.O=P(O)(O)O.[K]>CC(C)c1cc(C(C)C)c(-c2ccccc2[PH](C2CCCCC2)(C2CCCCC2)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)c(C(C)C)c1.CS(C)=O.O>CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(-c3cn(S(=O)(=O)c4ccccc4)c4ncccc34)c(C)cc21

Participants

9

Reactant 2

HCID 24805585tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 455881371-(Phenylsulfonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine

Product 3

HCID 7095BiphenylHCID 24805585tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 178474764HCID 178474764, compound

Reagents, catalysts & solvents 4

HCID 178439024HCID 178439024, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent2×HCID 16218557Phosphoric acid (potassium)Other

Workup

  1. additionAfter 22 hours the crude reactions were diluted with 3 x 1 uL 0.5 M AcOH in DMSO (containing PhPh as an internal standard). The reactions were mixed after each dispense operation.
  2. aliquotMosquito(R) was used to transfer 1 uL of each quenched reaction from the 1,536-well reaction plate to 384-well analytical plates containing 60 uL DMSO for analysis.

Sources & evidence

ORD record
ord-0754b2797e6b420b9e4b11699a52cf79
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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