Dibutyltin dichloride → HCID 67442271, compound

HRID 1400924Notes

Reaction equation

HRID 1400924 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH:30]=O)=[CH:26][N:25]=5)[S:23][C:16]=34)=[C:10]([F:32])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1.[O:33]1[CH2:38][CH2:37][N:36]([CH2:39][CH2:40][O:41][C:42]2[CH:48]=[CH:47][C:45]([NH2:46])=[CH:44][CH:43]=2)[CH2:35][CH2:34]1.C([Sn](Cl)(Cl)CCCC)CCC.C1([SiH3])C=CC=CC=1>CN(C=O)C.[Cl-].[Na+].O>[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][NH:46][C:45]6[CH:47]=[CH:48][C:42]([O:41][CH2:40][CH2:39][N:36]7[CH2:35][CH2:34][O:33][CH2:38][CH2:37]7)=[CH:43][CH:44]=6)=[CH:26][N:25]=5)[S:23][C:16]=34)=[C:10]([F:32])[CH:9]=2)=[O:6])[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 12688Dibutyltin dichlorideHCID 12752PhenylsilaneHCID 64847114-(2-Morpholinoethoxy)anilineHCID 582365791-Cyclopropyl-3-(3-fluoro-4-(2-(5-formylpyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)phenyl)urea

Product 1

HCID 67442271HCID 67442271, compoundYield 59.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of the aldehyde 47 (0.161 g, 0.359 mmol), 4-(2-morpholinoethoxy)aniline (0.120 g, 0.540 mmol), and dibutyltin dichloride (0.197 g, 0.648 mmol) in DMF (5 mL) was added a solution of phenylsilane (0.047 g, 0.434 mmol) in DMF (2 mL). The reaction mixture was stirred for 3 hours at RT and treated with a mixture of brine/sat. NAHCO3 solution. A precipitate was formed which was collected by filtration, washed with water and dried. Crude material was purified by flash column chromatography, eluent a 10 to 20% gradient of MeOH in AcOEt—to afford the title compound 331 (139 mg, 59.1% yield). 1H NMR (400 MHz, DMSO-d6) δ (ppm): 8.72 (s, 1H); 8.62 (d, J=1.6 Hz, 1H); 8.51 (dd, J=5.5 Hz, 1H); 8.30 (s, 1H); 8.22 (d, J=8.2 Hz, 1H); 7.88 (dd, J=8.2, 2.2 Hz, 1H); 7.73 (dd, J=13.5, 2.5 Hz, 1H); 7.38 (t, J=9.2 Hz, 1H); 7.20 (dd, J=8.8 1.2 Hz, 1H); 6.72-6.69 (m, 2H); 6.63 (dd, J=5.5, 0.8 Hz 1H); 6.58-6.54 (m, 3H); 5.95 (t, J=6.3 Hz, 1H); 4.30 (d, J=6.1 Hz, 2H); 3.82 (t, J=5.9 Hz, 2H); 3.55 (t, J=4.5 Hz, 4H); 2.60 (t, J=5.7 Hz, 2H); 2.57-2.62 (m, 1H); 2.42 (t, J=4.5 Hz, 4H); 0.68-0.63 (m, 2H); 0.47-0.41 (m, 2H). MS (m/z): 655.6 (M+1)+

Workup

  1. customA precipitate was formed which
  2. filtrationwas collected by filtration
  3. washwashed with water
  4. customdried
  5. customCrude material was purified by flash column chromatography, eluent a 10 to 20% gradient of MeOH in AcOEt—

Sources & evidence

ORD record
ord-bbb5ed46f9ce47ad80ae17431c21f07c
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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