2-Bromopyridine → 2-[(S)-1-Phenylethylamino]-4-[6-(4-(pyridine-2-yl)triazol-1-yl)benzimidazol-1-yl]pyrimidine

HRID 2300818Notes

Reaction equation

HRID 2300818 reaction equation
[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([N:25]5[CH:29]=[C:28]([Sn](CCCC)(CCCC)CCCC)[N:27]=[N:26]5)[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Br[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=1>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>[C:1]1([C@@H:7]([NH:9][C:10]2[N:15]=[C:14]([N:16]3[C:20]4[CH:21]=[C:22]([N:25]5[CH:29]=[C:28]([C:44]6[CH:49]=[CH:48][CH:47]=[CH:46][N:45]=6)[N:27]=[N:26]5)[CH:23]=[CH:24][C:19]=4[N:18]=[CH:17]3)[CH:13]=[CH:12][N:11]=2)[CH3:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

4

Reactant 2

HCID 79732-BromopyridineHCID 699625732-[(S)-1-phenylethylamino]-4-[6-(4-tributylstannyl-triazol-1-yl)benzimidazol-1-yl]pyrimidine

Product 1

HCID 599247812-[(S)-1-Phenylethylamino]-4-[6-(4-(pyridine-2-yl)triazol-1-yl)benzimidazol-1-yl]pyrimidineYield 9.6%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

The title compound was prepared from 30.5 mg of 2-[(S)-1-phenylethylamino]-4-[6-(4-tributylstannyl-triazol-1-yl)benzimidazol-1-yl]pyrimidine, 36.3 mg 2-bromopyridine and 0.5 mg Pd(PPh3)4 using the procedure described in EXAMPLE 273 except that the the reaction mixture was stirred for 16 hours. The residue was purified by flash chromatography eluting with acetone in hexanes to give 2.0 mg of the title compound. 1H NMR (500 MHz, 1:1 CD3OD/CDCl3): δ 1.64 (d, J=6.8 Hz, 3H), 5.28 (m, 1H), 7.0-7.35 (m, 5H), 7.40 (br s, 6.4 Hz, 1H), 7.54 (t, J=7.1 Hz, 1H), 7.84 (m, 1H), 7.93 (d, J=8.4 Hz, 1H), 8.11 (t, J=7.5 Hz, 1H), 8.32 (d, J=8.3 Hz, 1H), 8.36 (m, 1H), 8.65 (d, J=4.6 Hz, 1H), 8.83-9.2 (m, 3H). Mass Spectrum (CH3CN-TFA-NH4HCO2-ESI): 460.2 (M+1).

Workup

  1. customThe residue was purified by flash chromatography
  2. washeluting with acetone in hexanes

Sources & evidence

ORD record
ord-e4f10b88a07e449a9dfc9f1c9f461736
Source dataset
uspto-grants-2002_12
Patent number
US06498165B1

Reaction notes

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