Sodium Carbonate → 5-[2-Fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinamine

HRID 423643Notes

Reaction equation

HRID 423643 reaction equation
[NH2:1][C:2]1[CH:7]=[N:6][C:5](Br)=[CH:4][N:3]=1.[F:9][C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=1B(O)O.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.CO.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:9][C:10]1[CH:15]=[C:14]([S:16]([CH3:19])(=[O:18])=[O:17])[CH:13]=[CH:12][C:11]=1[C:5]1[N:6]=[CH:7][C:2]([NH2:1])=[N:3][CH:4]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 5995392-Amino-5-bromopyrazineHCID 447176662-Fluoro-4-(methylsulphonyl)benzeneboronic acid

Product 1

HCID 666732195-[2-Fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinamine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

5-[2-Fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinamine (0.30 g, 50%) was prepared as a yellowish brown solid from 2-amino-5-bromopyrazine (0.4 g, 2.23 mmol), [2-fluoro-4-(methylsulfonyl)phenyl]boronic acid (0.50 g, 2.23 mmol), 2M Na2CO3 (4 mL), Pd(PPh3)4 (52 mg, 0.05 mmol) in 1,4-dioxane (8 mL) and MeOH (4 mL) in a manner similar to Example 145, Step 1. The crude product was triturated with CH2Cl2 to give 5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinamine as a yellowish brown solid. 1H NMR (400 MHz, DMSO-d6): δ 8.41 (s, 1H), 8.11 (t, 1H, J=8.0 Hz), 8.01 (s, 1H), 7.85-7.75 (m, 2H), 6.91 (s, 2H), 3.26 (s, 3H); LRMS (ESI), m/z 268 (M+H).

Workup

  1. customThe crude product was triturated with CH2Cl2

Sources & evidence

ORD record
ord-24d243be51da4ad59b4ded9aa21e1abc
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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