Potassium Phosphate, Tribasic → HCID 86640995, compound

HRID 1972178Notes

Reaction equation

Br[C:2]1[C:3]([O:27][C:28]2[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=2)=[CH:4][C:5]([NH:8][C:9]2[S:10][CH:11]=[C:12]([CH:14]3[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]3)[N:13]=2)=[N:6][CH:7]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH3:85][O:86][C:87]1[CH:88]=[C:89]([SH:93])[CH:90]=[CH:91][CH:92]=1>C1(C)C=CC=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:85][O:86][C:87]1[CH:88]=[C:89]([S:93][C:2]2[C:3]([O:27][C:28]3[C:29]([CH3:34])=[N:30][CH:31]=[CH:32][CH:33]=3)=[CH:4][C:5]([NH:8][C:9]3[S:10][CH:11]=[C:12]([CH:14]4[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]4)[N:13]=3)=[N:6][CH:7]=2)[CH:90]=[CH:91][CH:92]=1

Participants

Conditions

Temperature: 130 °C

Procedure

tert-Butyl 4-(2-(5-bromo-4-(2-methylpyridin-3-yloxy)pyridin-2-ylamino)thiazol-4-yl)piperidine-1-carboxylate (0.15 g, 0.27 mmol), Pd2dba3 (0.25 g, 0.27 mmol), Xantphos (0.20 g, 0.34 mmol), and K3PO4 (0.175 g, 0.823 mmol) were suspended in degassed toluene (2 mL). 3-Methoxybenzenethiol (0.068 mL, 0.55 mmol) was added. The mixture was stirred at 130° C. for 3 hours in a sealed tube. The solution was cooled and flash chromatographed (40-50% EtOAc/hexanes) to afford the title compound (0.084 g, 51% yield) as an off-white solid.

Workup

temperatureThe solution was cooled
customflash chromatographed (40-50% EtOAc/hexanes)

Sources & evidence

ORD record: ord-4fb979f423294dc592cae31ee8f990e2
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08431713B2

Reaction notes

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