Potassium Phosphate, Tribasic → HCID 42636016, compound

HRID 1971000Notes

Reaction equation

HRID 1971000 reaction equation
[CH:1]1([CH:4]([NH:8][C:9]2[C:21]3[C:20]4[CH:19]=[CH:18][C:17](B5OC(C)(C)C(C)(C)O5)=[CH:16][C:15]=4[NH:14][C:13]=3[C:12]([C:31]([NH2:33])=[O:32])=[CH:11][N:10]=2)[CH:5]2[CH2:7][CH2:6]2)[CH2:3][CH2:2]1.Cl[C:35]1[N:36]=[N:37][CH:38]=[CH:39][CH:40]=1.C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.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]>[CH:1]1([CH:4]([NH:8][C:9]2[C:21]3[C:20]4[CH:19]=[CH:18][C:17]([C:35]5[N:36]=[N:37][CH:38]=[CH:39][CH:40]=5)=[CH:16][C:15]=4[NH:14][C:13]=3[C:12]([C:31]([NH2:33])=[O:32])=[CH:11][N:10]=2)[CH:5]2[CH2:6][CH2:7]2)[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 112749893-ChloropyridazineHCID 59543131HCID 59543131, compound

Product 1

HCID 42636016HCID 42636016, compound

Reagents, catalysts & solvents 2

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 1-[(dicyclopropylmethyl)amino]-7-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5H-pyrido[4,3-b]indole-4-carboxamide (30 mg, 0.067 mmol), 3-chloropyridazine (12 mg, 0.10 mmol), Pd2(dba)3 (6.2 mg, 0.0067 mmol), tricyclohexylphosphine (4.7 mg, 0.017 mmol), and K3PO4 (1.27 M, 220 μL, 0.27 mmol) in dioxane (1.3 mL) was purged with nitrogen for 10 min, heated to 100° C. for 3 h, and cooled to room temperature. The mixture was concentrated, and purified by flash chromatography to afford the title compound. 1H NMR (600 MHz, CD3SOCD3) δ 11.75 (s, 1H); 9.21 (d, 1H); 8.56 (d, 1H); 8.55 (s, 1H); 8.49 (s, 1H); 8.24 (d, 1H); 8.03 (d, 1H); 7.85 (br s, 1H); 7.81 (dd, 1H); 7.18 (br s, 1H); 6.66 (d, 1H); 3.65 (m, 1H); 1.40 (m, 2H); 0.55 (m, 2H); 0.37 (m, 6H). LRMS (APCI) calc'd for (C23H22N6O) [M+H]+, 399.2. found 399.1.

Workup

  1. customwas purged with nitrogen for 10 min
  2. temperaturecooled to room temperature
  3. concentrationThe mixture was concentrated
  4. custompurified by flash chromatography

Sources & evidence

ORD record
ord-88cd1f73ba3741faa4bdf775cf88bb32
Source dataset
uspto-grants-2013_04
Patent number
US08431569B2

Reaction notes

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