Dichloromethane → HCID 90310809, compound

HRID 1519178Notes

Reaction equation

HRID 1519178 reaction equation
[Si:1]([O:8][C:9]1[C:10]([F:24])=[C:11](B(O)O)[CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Br[C:26]1[N:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=1.C([O-])([O-])=O.[K+].[K+].C(Cl)Cl>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].C1(C)C=CC=CC=1>[Si:1]([O:8][C:9]1[C:10]([F:24])=[C:11]([C:26]2[N:27]=[CH:28][C:29]([NH2:32])=[N:30][CH:31]=2)[CH:12]=[CH:13][C:14]=1[CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6344DichloromethaneHCID 11430Potassium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 90310646HCID 90310646, compound

Product 1

HCID 90310809HCID 90310809, compoundYield 101.3%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of (3-((tert-butyldimethylsilyl)oxy)-4-cyclohexyl-2-fluorophenyl)boronic acid (0.821 g, 2.33 mmol), 5-bromopyrazin-2-amine (0.40 g, 2.3 mmol), K2CO3 (0.659 g, 4.77 mmol), Pd(dppf)Cl2.CH2Cl2 (0.086 g, 0.12 mmol), deoxygenated toluene (10 mL), and deoxygenated deionized water (10 mL) was heated for 16 hours at 80° Celsius. The reaction mixture was then cooled to rt, diluted with dichloromethane (25 mL), and washed with brine (2×25 mL). The organic layer was dried over MgSO4, filtered, and concentrated to dryness to yield the title compound (0.936 g, 100%) which was used without purification.

Workup

  1. customdeoxygenated deionized water (10 mL)
  2. temperatureThe reaction mixture was then cooled to rt
  3. additiondiluted with dichloromethane (25 mL)
  4. washwashed with brine (2×25 mL)
  5. dry with materialThe organic layer was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-04a166a5c79d43aeb039fc89d76e895b
Source dataset
uspto-grants-2015_07
Patent number
US09073876B2

Reaction notes

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