2,2'-Bis(dicyclohexylphosphino)-1,1'-biphenyl → HCID 68779547, compound

HRID 1889858Notes

Reaction equation

HRID 1889858 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]3[N:17]=[C:18]([NH2:20])[N:19]=[C:15]3[CH:14]=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].Br[C:22]1[CH:23]=[C:24]([CH:34]=[CH:35][CH:36]=1)[CH2:25][N:26]1[CH2:31][CH2:30][S:29](=[O:33])(=[O:32])[CH2:28][CH2:27]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)CCCCC1>>[O:33]=[S:29]1(=[O:32])[CH2:30][CH2:31][N:26]([CH2:25][C:24]2[CH:23]=[C:22]([NH:20][C:18]3[N:19]=[C:15]4[CH:14]=[CH:13][CH:12]=[C:11]([C:8]5[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:3])=[O:4])=[CH:6][CH:7]=5)[N:16]4[N:17]=3)[CH:36]=[CH:35][CH:34]=2)[CH2:27][CH2:28]1

Participants

4

Reactant 3

HCID 249469872,2'-Bis(dicyclohexylphosphino)-1,1'-biphenylHCID 60584697HCID 60584697, compoundHCID 674790495-(4-(Methylsulfonyl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 68779547HCID 68779547, compound

Procedure

N-{3-[(1,1-dioxidothiomorpholin-4-yl)methyl]phenyl}-5-[4-(methylsulfonyl)phenyl][1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from 5-(4-methanesulfonyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (75.0 mg, 0.260 mmol) and 4-(3-bromo-benzyl)-thiomorpholine 1,1-dioxide (90.0 mg, 0.296 mmol) with 2,2′-bis-dicyclohexylphosphanyl-biphenyl (25.0 mg, 0.0457 mmol) as the ligand in a manner analogous to Example 2d. Product isolated as a yellow foam (0.042 g, 32%). 1H NMR (400 MHz, CDCl3, δ, ppm): 8.26 (d, J=8.5 Hz, 2H), 8.14 (d, J=8.5 Hz, 2H), 7.45 (dd, J=8.2, 1.8 Hz, 1H), 7.30 (t, J=7.7 Hz, 1H), 7.07 (t, J=4.3 Hz, 1H), 6.96-6.91 (m, 2H), 3.65 (s, 2H), 3.16 (s, 3H), 3.07-2.97 (m, 8H). MS=512 (MH)+.

Sources & evidence

ORD record
ord-7a7fd0e1204d42959cd703d23bf55f27
Source dataset
uspto-grants-2013_08
Patent number
US08501936B2

Reaction notes

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