Potassium Phosphate, Tribasic → HCID 178494859, compound

HRID 1432076Notes

Reaction equation

OC(C(F)(F)F)=O.Br[C:9]1[CH:10]=[C:11]([CH:33]=[C:34]([Cl:36])[CH:35]=1)[CH2:12][NH:13][C:14]([NH2:32])=[N:15][C:16]([C:18]1[C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[N:20][O:21][C:22]=1[CH3:23])=[O:17].[CH3:37][O:38][CH2:39]/[CH:40]=[CH:41]/B1OC(C)(C)C(C)(C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[Cl:36][C:34]1[CH:33]=[C:11]([CH:10]=[C:9](/[CH:41]=[CH:40]/[CH2:39][O:38][CH3:37])[CH:35]=1)[CH2:12][NH:13][C:14]([NH2:32])=[N:15][C:16]([C:18]1[C:19]([C:24]2[CH:29]=[CH:28][C:27]([O:30][CH3:31])=[CH:26][CH:25]=2)=[N:20][O:21][C:22]=1[CH3:23])=[O:17]

Participants

Conditions

Temperature: 85 °C

Procedure

A mixture of N-((3-Bromo-5-chlorobenzylamino)(amino)methylene)-3-(4-methoxyphenyl)-5-methylisoxazole-4-carboxamide TFA salt (˜10-15 mg) (Prepared by analogy to Example 1), (E)-2-(3-methoxypropenyl)-4,4,5,5,-tetramethyl-(1,3,2)-dioxaborolane (20 mg), tetrakis-(triphenylphosphine)-palladium (5 mg) and aqueous tripotassium phosphate (2M, 100 μl) in DMF (1 mL) was heated at 85° C. under nitrogen overnight. Product was obtained by HPLC purification. 1H NMR (CD3OD): δ 2.69 (s, 3H), 3.40 (s, 3H), 3.86(s, 3H), 4.11, 4.13(d, 2H), 4.58(s, 2H), 6.44(m, 1H), 6.64, 6.67(d, 1H), 7.05, 7.07(d, 2H), 7.29 (s, 1H), 7.37(s,1 H), 7.46 (s, 1H), 7.62, 7.64(d, 2H). MH+=469.23

Workup

customProduct was obtained by HPLC purification

Sources & evidence

ORD record: ord-113fc802035b4af39f877862ce3f37d0
Source dataset: uspto-grants-2009_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07612069B2

Reaction notes

Loading…