2-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenyl → HCID 71255244, compound

HRID 540128Notes

Reaction equation

HRID 540128 reaction equation
[CH2:1]1[C:4]2([CH:8]([NH:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][NH:6][CH2:5]2)[CH2:3][O:2]1.Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[C:25](OC(F)(F)F)[CH:26]=2)[N:21]=[C:20]([N:33]2[CH2:39][C:38]3[CH:40]=[CH:41][CH:42]=[CH:43][C:37]=3[S:36](=[O:45])(=[O:44])[CH2:35][CH2:34]2)[CH:19]=1.[CH:46]1(P(C2CCCCC2)C2C=CC=CC=2C2C(N(C)C)=CC=CC=2)CCCCC1.CC(C)([O-])C.[Na+]>C(OCC)(=O)C.O1CCOCC1>[O:44]=[S:36]1(=[O:45])[C:37]2[CH:43]=[CH:42][CH:41]=[CH:40][C:38]=2[CH2:39][N:33]([C:20]2[CH:19]=[C:18]([N:6]3[CH2:7][CH:8]([NH:9][C:10]([O:11][C:12]([CH3:13])([CH3:15])[CH3:14])=[O:16])[C:4]4([CH2:3][O:2][CH2:1]4)[CH2:5]3)[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([CH3:46])[CH:26]=3)[N:21]=2)[CH2:34][CH2:35]1

Participants

7

Reactant 4

HCID 27342172-(Dicyclohexylphosphino)-2'-(dimethylamino)biphenylHCID 23676156Sodium t-butoxideHCID 71254567HCID 71254567, compoundHCID 712545694-(4-Chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide

Product 1

HCID 71255244HCID 71255244, compoundYield 925.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of tert-butyl 2-oxa-6-azaspiro[3.4]oct-8-ylcarbamate (459 mg, 2.0 mmol), 4-(4-chloro-6-methylquinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide (500 mg, 1.34 mmol, prepared in analogy to 4-(4-chloro-6-(trifluoromethoxy)quinolin-2-yl)-2,3,4,5-tetrahydro-1,4-benzothiazepine 1,1-dioxide in Example 17-1 by using 2,4-dichloro-6-methylquinoline and 2,3,4,5-tetrahydro-1,4-benzothiazepine 1,2-dioxide), tri(dibenzylideneacetone)dipalladium(0) (61.3 mg, 0.067 mmol), 2′-(dicyclohexylphosphino)-N,N-dimethyl[1,1′-biphenyl]-2-amine (52.7 mg, 0.134 mmol), sodium tert-butoxide (192.2 mg, 2.0 mmol) and 1,4-dioxane (6 mL) was heated with stirring in a 20 mL of microwave process vial for 3 hours at 100° C. The mixture was diluted with ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography on silica gel to give 700 mg of the product as a white solid, which was used for next step without further purification.

Workup

  1. temperaturewas heated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-f8f7b6db07e34a03adf417136ffbffc5
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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