Potassium Phosphate, Tribasic → (1S,2S,3S)-3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]-2-hydroxy-1-methyl-cyclohexanecarboxylic acid

HRID 75029Notes

Reaction equation

HRID 75029 reaction equation
[H][H].ClC1C=C2C(B3OC(C)(C)[C:15](C)(C)[O:14]3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.[CH3:32][CH2:33][N:34](C(C)C)C(C)C.[Cl:41][C:42]1[CH:43]=[C:44]2[C:50]([C:51]3[N:56]=[C:55](S(C)=O)[C:54]([F:60])=[CH:53][N:52]=3)=[CH:49][N:48](S(C3C=CC(C)=CC=3)(=O)=O)[C:45]2=[N:46][CH:47]=1.[CH3:71]C(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:113]1[CH2:117][O:116][CH2:115][CH2:114]1.[OH2:118]>[Pd].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].O.C1COCC1.CCN(CC)CC.CCO>[Cl:41][C:42]1[CH:43]=[C:44]2[C:50]([C:51]3[N:56]=[C:55]([NH:34][C@H:33]4[CH2:32][CH2:115][CH2:114][C@:113]([CH3:71])([C:15]([OH:14])=[O:118])[C@@H:117]4[OH:116])[C:54]([F:60])=[CH:53][N:52]=3)=[CH:49][NH:48][C:45]2=[N:46][CH:47]=1

Participants

14

Reactant 7

HCID 62657Potassium Phosphate, TribasicHCID 81531DiisopropylethylamineHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 21881883Oxolane--water (1/1)HCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine2×HCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine3×HCID 178418361HCID 178418361, compound

Product 1

HCID 68008179(1S,2S,3S)-3-[[2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoro-pyrimidin-4-yl]amino]-2-hydroxy-1-methyl-cyclohexanecarboxylic acid

Reagents, catalysts & solvents 6

HCID 23938PalladiumCatalystHCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8471TriethylamineSolvent

Procedure

Pd/C (wet, Degussa), hydrogen, EtOH; (b) 2,4-dichloro-5-fluoropyrimidine, iPr2NEt, THF, reflux; (c) LiOH, THF/water, 50° C.; (d) DPPA, Et3N, THF, 85° C.; (e) 5-fluoro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, XPhos, Pd2(dba)3, K3PO4, 2-methyl THF, water, 125° C.; (f)

Sources & evidence

ORD record
ord-34a36f2102c4460d8cf16149aea07d0c
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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