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

HRID 608082Notes

Reaction equation

HRID 608082 reaction equation
CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(Cl)c(C)cc21.CC(C)(C)N=P(N1CCCC1)(N1CCCC1)N1CCCC1.Cc1cc(O)ccc1B1OC(C)(C)C(C)(C)O1>CCC(C)(C)O.CN(C)c1ccc([PH](C(C)(C)C)(C(C)(C)C)[Pd]2([O]S(C)(=O)=O)[NH]c3ccccc3-c3cccc[c]32)cc1.CS(C)=O.O>CC(=O)NC(C)(C)[C@@H]1CC2(CCN(C(=O)OC(C)(C)C)CC2)c2cc(-c3ccc(O)cc3C)c(C)cc21

Participants

10

Reactant 2

HCID 24805585tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4'-piperidine]-1'-carboxylateHCID 574432723-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

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 178474761HCID 178474761, compound

Reagents, catalysts & solvents 5

HCID 178482905HCID 178482905, compoundCatalystHCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolventHCID 64052-Methyl-2-butanolSolventHCID 3856267tert-Butylimino-tri(pyrrolidino)phosphoraneOther

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-8316a2d7a1854cffac7b5eca64453cea
Source dataset
Cernak miniaturized Suzuki Cross-Coupling 12x10 Informer Library
Original link
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Reaction notes

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