Potassium Phosphate, Tribasic → HCID 66604777, compound

HRID 2410901Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]([C:23]([NH2:25])=[O:24])[C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([C:15]([N:17]4[CH2:22][CH2:21][O:20][CH2:19][CH2:18]4)=[O:16])=[CH:11][C:12]=3[C:13]=2[N:14]=1.[C:26]1(B(O)O)[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[O-]P([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1COCC1>[N:17]1([C:15]([C:10]2[CH:9]=[CH:8][C:7]3[NH:6][C:5]4[C:4]([C:23]([NH2:25])=[O:24])=[CH:3][C:2]([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)=[N:14][C:13]=4[C:12]=3[CH:11]=2)=[O:16])[CH2:22][CH2:21][O:20][CH2:19][CH2:18]1

Participants

Conditions

Temperature: 85 °C

Procedure

2-Bromo-8-(morpholine-4-carbonyl)-5H-pyrido[3,2-b]indole-4-carboxamide (100 mg, 0.248 mmol), phenylboronic acid (60.5 mg, 0.496 mmol), potassium phosphate tribasic (168 mg, 0.794 mmol), 2-Dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (23.64 mg, 0.050 mmol) and palladium(II) acetate (5.57 mg, 0.025 mmol) were mixed with THF (4 mL) in a sealed microwave tube. The mixture was heated in microwave at 85° C. for 3 hrs. The mixture was concentrated and purified using preparative HPLC to give titled product. MS (ESI) m/z 401.2 (M+H)+. 1H NMR (DMSO-d6) δ ppm 11.8 (s, 1H), 8.65 (s, 1H), 8.5 (s, 1H), 8.32 (m, 3H), 7.94 (s, 1H), 7.81(d, 1H, J=8.2), 7.60(m, 3H), 7.44 (t, 1H, J=7), 3.7-3.5 (bm, 8H).

Workup

concentrationThe mixture was concentrated
custompurified

Sources & evidence

ORD record: ord-61b43d301e984034afba85dd8bef10fc
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815840B2

Reaction notes

Loading…