Dichloromethane → HCID 178437110, compound

HRID 1484898Notes

Reaction equation

HRID 1484898 reaction equation
C(Cl)Cl.[C:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14](B2OC(C)(C)C(C)(C)O2)[CH:13]=1)(=[O:11])=[O:10])([CH3:7])([CH3:6])[CH3:5].Br[C:28]1[N:33]=[C:32]([NH:34][C:35]2[CH:39]=[C:38]([CH:40]3[CH2:42][CH2:41]3)[NH:37][N:36]=2)[C:31]([C:43]#[C:44][Si](C)(C)C)=[CH:30][N:29]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[C:4]([NH:8][S:9]([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:28]2[N:33]=[C:32]([NH:34][C:35]3[NH:36][N:37]=[C:38]([CH:40]4[CH2:42][CH2:41]4)[CH:39]=3)[C:31]([C:43]#[CH:44])=[CH:30][N:29]=2)[CH:13]=1)(=[O:10])=[O:11])([CH3:5])([CH3:6])[CH3:7]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 10340Sodium CarbonateHCID 58169119N-tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamideHCID 58169125HCID 58169125, compound

Product 1

HCID 178437110HCID 178437110, compoundYield 23%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of Pd(dppf)Cl2.CH2Cl2 (65.3 mg, 0.08 mmol, 0.1 equiv.), N-tert-butyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenesulfonamide (542 g, 1.60 mmol, 2.0 equiv.), 2-Bromo-N-(5-cyclopropyl-1H-pyrazol-3-yl)-5-((trimethyl silyl)ethynyl) pyrimidin-4-amine (300 mg, 0.80 mmol, 1.0 equiv.) and saturated aq Na2CO3 (10 mL) in dioxane (30 mL) was heated to 90° C. for 1 h under nitrogen atmosphere. The reaction mixture was cooled to room temperature and extracted with THF. The combined layers were concentrated and the residue was purified by silica gel chromatography (EtOAc/Petroleum ether from 10:1 to 1:1) to afford compound N-tert-butyl-3-(4-(3-cyclopropyl-1H-pyrazol-5-ylamino)-5-ethynylpyrimidin-2-yl)benzenesulfonamide (80 mg, 23%). LC-MS (m/z)=437.1 [M+H]+.

Workup

  1. extractionextracted with THF
  2. concentrationThe combined layers were concentrated
  3. customthe residue was purified by silica gel chromatography (EtOAc/Petroleum ether from 10:1 to 1:1)

Sources & evidence

ORD record
ord-f1aced7daf014f3f9dcdea71b64a1e49
Source dataset
uspto-grants-2016_08
Patent number
US09422271B2

Reaction notes

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