Sodium Carbonate → (2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

HRID 74950Notes

Reaction equation

HRID 74950 reaction equation
ClC1[N:7]=[C:6](Cl)[C:5](F)=[CH:4]N=1.ClC1C=C2C(B3O[C:23](C)([CH3:25])[C:22](C)(C)[O:21]3)=CN(S(C3C=CC(C)=CC=3)(=O)=O)C2=NC=1.C([O-])([O-])=[O:40].[Na+].[Na+].[Cl:45][C:46]1[CH:47]=[C:48]2[C:54]([C:55]3[N:60]=[C:59](S(C)=O)[C:58]([F:64])=[CH:57][N:56]=3)=[CH:53][N:52](S(C3C=CC(C)=CC=3)(=O)=O)[C:49]2=[N:50][CH:51]=1>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1COCC1.C(#N)C.C(O)(C)C>[Cl:45][C:46]1[CH:47]=[C:48]2[C:54]([C:55]3[N:60]=[C:59]([NH:7][C:6]4([OH:40])[CH2:5][CH2:4][CH2:25][CH2:23][CH:22]4[OH:21])[C:58]([F:64])=[CH:57][N:56]=3)=[CH:53][NH:52][C:49]2=[N:50][CH:51]=1

Participants

9

Reactant 4

HCID 10340Sodium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 575977475-Chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 672853215-Chloro-3-(5-fluoro-4-methylsulfinyl-pyrimidin-2-yl)-1-(p-tolylsulfonyl)pyrrolo[2,3-b]pyridine

Product 1

HCID 86762729(2-(5-chloro-1H-pyrrolo[2,3-b]pyridin-3-yl)-5-fluoropyrimidin-4-ylamino)cyclohexane-1,2-diol

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 3776IsopropanolSolventHCID 6342AcetonitrileSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2,4-dichloro-5-fluoropyrimidine, acetonitrile, isopropanol, reflux 1.5 hours; (b) 5-chloro-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine, Pd(PPh3)4, 2M Na2CO3, acetonitrile, 120° C. microwave, 15 min.; (c) TBAF, THF.

Sources & evidence

ORD record
ord-3e56024df82a4c45b22cc6ae611ea9d4
Source dataset
uspto-grants-2014_09
Patent number
US08829007B2

Reaction notes

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