Formaldehyde → HCID 118524051, compound

HRID 531873Notes

Reaction equation

HRID 531873 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]([C:59]2[CH:60]=[C:61]3[C:67]([C:68]4[CH:69]=[N:70][N:71]([CH2:73][C:74]5[CH:79]=[CH:78][CH:77]=[C:76]([F:80])[CH:75]=5)[CH:72]=4)=[CH:66][N:65]([S:81]([C:84]4[CH:90]=[CH:89][C:87]([CH3:88])=[CH:86][CH:85]=4)(=[O:83])=[O:82])[C:62]3=[N:63][CH:64]=2)[CH:50]=[N:51][C:52]=1[N:53]1[CH2:58][CH2:57][NH:56][CH2:55][CH2:54]1.C=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(O)(=O)C.ClC(Cl)C>[F:46][C:47]1[CH:48]=[C:49]([C:59]2[CH:60]=[C:61]3[C:67]([C:68]4[CH:69]=[N:70][N:71]([CH2:73][C:74]5[CH:79]=[CH:78][CH:77]=[C:76]([F:80])[CH:75]=5)[CH:72]=4)=[CH:66][N:65]([S:81]([C:84]4[CH:90]=[CH:89][C:87]([CH3:88])=[CH:86][CH:85]=4)(=[O:82])=[O:83])[C:62]3=[N:63][CH:64]=2)[CH:50]=[N:51][C:52]=1[N:53]1[CH2:58][CH2:57][N:56]([CH3:3])[CH2:55][CH2:54]1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 1185240853-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-5-(4-(piperidin-4-yl)phenyl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine hydrochlorideHCID 118524115HCID 118524115, compound

Product 1

HCID 118524051HCID 118524051, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

Using similar reaction conditions as described in step-iii of example-133, 5-(5-fluoro-6-(piperazin-1-yl)pyridin-3-yl)-3-(1-(3-fluorobenzyl)-1H-pyrazol-4-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine (170 mg, 0.272 mmol) was methylated using paraformaldehyde (24 mg, 0.816 mmol), Na(OAc)3BH (172 mg, 0.816 mmol) and 3 drops of acetic acid in dichloroethane (10 mL) to afford 154 mg (89% yield) of the titled compound. MS: m/z=640.6 (M+1).

Workup

  1. customreaction conditions

Sources & evidence

ORD record
ord-74b9f4c72fb94f1e8537e8e061afd040
Source dataset
uspto-grants-2016_05
Patent number
US09353107B2

Reaction notes

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