Formaldehyde → 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine

HRID 531763Notes

Reaction equation

HRID 531763 reaction equation
Cl.F[C:3]1C=C(C=CC=1)CN1C=C(C2C3C(=NC=C(C4C=CC(C5CCNCC5)=CC=4)C=3)N(S(C3C=CC(C)=CC=3)(=O)=O)C=2)C=N1.[F:46][C:47]1[CH:48]=[C:49]([CH:87]=[CH:88][CH:89]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][NH:74][CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[N:58]([S:77]([C:80]3[CH:86]=[CH:85][C:83]([CH3:84])=[CH:82][CH:81]=3)(=[O:79])=[O:78])[CH:57]=2)[CH:53]=[N:52]1.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClC(Cl)C>[F:46][C:47]1[CH:48]=[C:49]([CH:87]=[CH:88][CH:89]=1)[CH2:50][N:51]1[CH:55]=[C:54]([C:56]2[C:64]3[C:59](=[N:60][CH:61]=[C:62]([C:65]4[CH:66]=[N:67][C:68]([N:71]5[CH2:76][CH2:75][N:74]([CH3:3])[CH2:73][CH2:72]5)=[CH:69][CH:70]=4)[CH:63]=3)[N:58]([S:77]([C:80]3[CH:86]=[CH:85][C:83]([CH3:84])=[CH:82][CH:81]=3)(=[O:79])=[O:78])[CH:57]=2)[CH:53]=[N:52]1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 900303003-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochloride

Product 1

HCID 900336343-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(4-methylpiperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridineYield 88.2%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-133, 3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(6-(piperazin-1-yl)pyridin-3-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (100 mg, 0.164 mmol) was methylated using paraformaldehyde (15 mg, 0.494 mmol) and Na(OAc)3BH (105 mg, 0.494 mmol) in dichloroethane (5 mL) to afford 90 mg (88.2% yield) of the titled compound after purification by column (Silica gel 60/120) using 5% methanol in dichloromethane as eluent. MS: m/z=622.1 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-3243d6c096d94ecd9097e504acf03e61
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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