Imidazole → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-(methylsulfonylmethyl)cyclohexanol

HRID 74979Notes

Reaction equation

HRID 74979 reaction equation
C[Al](C)C.C1C=CC(P(C2C=CC3C(=CC=CC=3)C=2[C:28]2[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.ClC1C=C2C(B3OC(C)(C)C(C)(C)O3)=CN([S:70]([C:73]3C=CC(C)=CC=3)(=[O:72])=[O:71])C2=NC=1.N1C=CN=C1.[Cl:85][C:86]1[CH:87]=[C:88]2[C:94]([C:95]3[N:100]=[C:99](S(C)=O)[C:98]([F:104])=[CH:97][N:96]=3)=[CH:93][N:92](S(C3C=CC(C)=CC=3)(=O)=O)[C:89]2=[N:90][CH:91]=1.[NH4+:115].[Cl-].CCN(C(C)C)C(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C[OH:145]>CN(C1C=CN=CC=1)C.[Pd].C1COCC1.CCOC(C)=O.C(Cl)Cl.CN(C=O)C>[Cl:85][C:86]1[CH:87]=[C:88]2[C:94]([C:95]3[N:100]=[C:99]([NH:115][CH:32]4[CH2:33][CH2:34][CH2:35][CH2:36][C:37]4([CH2:28][S:70]([CH3:73])(=[O:72])=[O:71])[OH:145])[C:98]([F:104])=[CH:97][N:96]=3)=[CH:93][NH:92][C:89]2=[N:90][CH:91]=1

Participants

16

Reactant 9

HCID 795ImidazoleHCID 887MethanolHCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 634876Binap, (A+-)-HCID 2724141Tetrabutylammonium FluorideHCID 16682925TrimethylaluminumHCID 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]pyridine2×

Product 1

HCID 86762731(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)-1-(methylsulfonylmethyl)cyclohexanol

Reagents, catalysts & solvents 6

HCID 142844-(Dimethylamino)pyridineCatalystHCID 23938PalladiumCatalystHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

AlMe3, [Rh2(cod)2Cl2], (S)-BINAP, THF, 0° C.; (b) TBSCl, imidazole, DMAP, DMF; (c) 3-chloroperoxybenzoic acid, CH2Cl2; (d) sodium azide, NH4Cl, MeOH, H2Ol; (e) H2, Pd—C (10%), EtOAc; (f) 5-chloro-3-(5-fluoro-4-(methylsulfinyl)pyrimidin-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, iPr2NEt, microwave, 70° C.; (g) TBAF, THF

Sources & evidence

ORD record
ord-16e1e161550c47389fac1658b23cab04
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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